Synthesis and reactions of some nitrone derivatives
β Scribed by Orazio A Attanasi; Paolino Filippone; Chiara Fiorucci
- Book ID
- 104207451
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 695 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
A~,lnitroso ccxnpounds c;isily react ;is nucleophilcs ~ith conjugated azoalkenes to give (~-(arylimino-N-oxide)hydraz~mes by their 1,4-addition to the a~x~-cnc system These adducts undergo an internal hetcr~x:yclizati~m process with pyra;/.ole ring formation to produce 1-alkoxycarbonyl-or I-amintx~lrtxmyl-3-methyl-4qarylimino-N~xidc)-IH-pyraz~-5(4H)-ones stereoselectively in Z form by loss of an alcohol molecule. Dcoxygenation of these complmnds with triphenylphosphine affords I-alkoxycarlx~nyl-or l-amin~x.'artxmyl-3-methyl-4-arylimino-IH-pyi-azx~l-5(4H)-ones. Basic treatment with triethylamine of the same comlxmnds leads to 3-rnethyl~l-(arylimino-N-oxidc)-lH-pyrazd-5(4H)ones by removal of the substltucnts on N( I ) hctcroatom of the pyrazolc ring. Both dcoxygenation and basic treatment of l-alkoxxcarbonyl-and 1 -amintx:artxmyl-3-methyl-4-(arylirnino-N-oxide)-lH-p)Tec/ol-5(4H)-ones have been realized sequentially, providing 3-methyl-4-arylimino-lH-pyr~x~l-5(4H)-tmcs. Thc same products were succcsfully obtai ned by rcvcrsing the order of thc~ processes.
π SIMILAR VOLUMES
## Abstract magnified image Reaction of __visnaginone__ **1** with allyl bromide gave __O__βallyl __visnaginone__ **2** which underwent Claisen rearrangement to yield 7βallylbenzofuran derivative **3**. Reaction of **3** with different aromatic aldehydes gave the corresponding 5βcinnamoylbenzofura
Condensation of different cyclic ketones with visnaginone la and khellinone lb afforded spirofurochromanone derivatives 2a-f. Compounds 2a and 2b were readily demethylated to give the compounds 3a and 3b. Nitration of 2b and 2e gave the nitrofurochromonone and quinone derivatives 4 and 5 respectivel